Synthesis of Spirooxindoles from N-Arylamide Derivatives via Oxidative C(sp2)-C(sp3) Bond Formation Mediated by PhI(OMe)2 Generated in Situ

Xiaohua Zhen; Xintong Wan; Wei Zhang; Qiao Li; Daisy Zhang-Negrerie; Yunfei Du

doi:10.1021/acs.orglett.8b03741

Synthesis of Spirooxindoles from N-Arylamide Derivatives via Oxidative C(sp²)-C(sp³) Bond Formation Mediated by PhI(OMe)₂ Generated in Situ

Org Lett. 2019 Feb 15;21(4):890-894. doi: 10.1021/acs.orglett.8b03741. Epub 2019 Jan 30.

Authors

Xiaohua Zhen¹, Xintong Wan¹, Wei Zhang¹, Qiao Li¹, Daisy Zhang-Negrerie¹, Yunfei Du^{1

2}

Affiliations

¹ Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology , Tianjin University , Tianjin 300072 , China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072 , China.

PMID: 30698442
DOI: 10.1021/acs.orglett.8b03741

Abstract

A class of novel spirooxindole compounds (2) were readily synthesized, in a metal-free environment, from N-arylamide derivatives (1) via intramolecular oxidative cyclization. Direct oxidative C(sp²)-C(sp³) bond formation was realized with the least-studied PhI(OMe)₂ as an oxidant, formed in situ from the reaction between PhIO and MeOH.

Publication types

Research Support, Non-U.S. Gov't